Diisopropylethylamine → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(3-fluoro-1-pyridyl)piperidine

HRID 845438

Reaktionsgleichung

Reaktionsgleichung von HRID 845438
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:22][C:23]1[C:24](Cl)=[N:25][CH:26]=[CH:27][CH:28]=1.C(N(C(C)C)C(C)C)C.C(N(CCC)CCC)C>C(O)CCC>[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH:16]3[CH2:17][CH2:18][N:19]([N:25]4[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH2:24]4)[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 519799N,N-DipropylethylamineHCID 27827912-Chloro-3-fluoropyridine2×HCID 137534104-(5H-Dibenzo[a,d][7]annulen-5-yl)piperidine

Produkt 1

HCID 201312374-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(3-fluoro-1-pyridyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

0.50 gram (1.82 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine, 0.24 gram (1.82 millimoles) of 3-fluoro-2-chloropyridine, 0.47 gram (3.64 mole) of ethyl diisopropylamine and 10 milliliters of n-butanol were heated at reflux temperature protected from atmospheric moisture with a drying tube. After 19.25 hours heating, an additional 240 milligrams of the 3-fluoro-2-chloropyridine was added. After another 24 hours, 300 milligrams of ethyl dipropylamine was added and heating continued. After about 140 hours of refluxing, the mixture was concentrated, diluted with ether, washed successively with 10 percent aqueous sodium hydroxide and brine, dried, and the solvent vaporized to obtain a brown semi-solid residue. The residue was purified by chromatographing on silica gel with 7 percent ether in hexanes to obtain the 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(3-fluoro-1-pyridyl)piperidine product as a crystalline white solid, which after drying overnight in vacuo and 4 hours at 100° C. at 1 millimeter of mercury pressure had a melting point of 208°-210° C. Elemental analyses were as follows:

Aufarbeitung

  1. temperatureat reflux temperature
  2. customprotected from atmospheric moisture with a drying tube
  3. temperatureAfter 19.25 hours heating
  4. temperatureheating
  5. temperatureAfter about 140 hours of refluxing
  6. concentrationthe mixture was concentrated
  7. additiondiluted with ether
  8. washwashed successively with 10 percent aqueous sodium hydroxide and brine
  9. customdried
  10. customto obtain a brown semi-solid residue
  11. customThe residue was purified by chromatographing on silica gel with 7 percent ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-108c710cdd00496ca88561e5d9ffd609
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758577

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